para–Phenylenediamine Dimer as a Redox–Active Guest for
Supramolecular Systems

J 2024

para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems

JANOVSKÝ, Petr; Andreas SPRINGER; Jaroslav FILIP; Zdeňka PRUCKOVÁ; Marek NEČAS et. al.

Základní údaje

Originální název

para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems

Autoři

JANOVSKÝ, Petr; Andreas SPRINGER; Jaroslav FILIP; Zdeňka PRUCKOVÁ; Marek NEČAS; Michal ROUCHAL; Christoph A SCHALLEY a Robert VICHA

Vydání

Chemistry - A European Journal, Wiley, 2024, 0947-6539

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.700

Kód RIV

RIV/00216224:14310/24:00138672

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.1002/chem.202400535

UT WoS

001188552000001

EID Scopus

2-s2.0-85188232192

Klíčová slova anglicky

cucurbiturils; cyclodextrins; host-guest systems; redox-active dye

Štítky

14313010, CF BIC, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 27. 3. 2025 08:05, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

Redox–active components are highly valuable in the construction of molecular devices. We combined two p-phenylenediamines (p-PDA) with a biphenyl (BiPhe) unit to prepare a supramolecular guest 4 consisting of three binding sites for cucurbit[7/8]uril (CBn) and/or cyclodextrins (CD). Supramolecular properties of 4 were investigated using NMR, UV-vis, mass spectrometry and isothermal titration calorimetry. Our analysis revealed that 4 forms higher–order host–guest complexes, wherein a CD unit occupies the central BiPhe site, secured by two CBn units at the terminal p-PDA sites. Additionally, 1 : 1 complexes with α-CD and β-CD, a 1 : 2 complex with γ-CD and 2 : 1 complexes with CB7 and CB8 were identified. Through UV-vis and cyclic voltammetry, redox processes leading to the formation of a stable, deep blue dication diradical of 4 are elucidated. Furthermore, it is demonstrated that CB7 selectively protects oxidised 4 from reduction in the presence of a reducing agent. The supramolecular and redox properties of the structural motif represented by 4 render it an interesting candidate for the construction of supramolecular devices.

Návaznosti

90242, velká výzkumná infrastruktura

Název: CIISB III

Citovat

JANOVSKÝ, Petr; Andreas SPRINGER; Jaroslav FILIP; Zdeňka PRUCKOVÁ; Marek NEČAS; Michal ROUCHAL; Christoph A SCHALLEY a Robert VICHA. para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems. Chemistry - A European Journal. Wiley, 2024, roč. 30, č. 25, s. 1-12. ISSN 0947-6539. Dostupné z: https://doi.org/10.1002/chem.202400535.

@article{2471980,
   author = {Janovský, Petr and Springer, Andreas and Filip, Jaroslav and Prucková, Zdeňka and Nečas, Marek and Rouchal, Michal and Schalley, Christoph A and Vicha, Robert},
   article_number = {25},
   doi = {https://doi.org/10.1002/chem.202400535},
   keywords = {cucurbiturils; cyclodextrins; host-guest systems; redox-active dye},
   language = {eng},
   issn = {0947-6539},
   journal = {Chemistry - A European Journal},
   title = {para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems},
   url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202400535},
   volume = {30},
   year = {2024}
}

TY  - JOUR
ID  - 2471980
AU  - Janovský, Petr - Springer, Andreas - Filip, Jaroslav - Prucková, Zdeňka - Nečas, Marek - Rouchal, Michal - Schalley, Christoph A - Vicha, Robert
PY  - 2024
TI  - para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems
JF  - Chemistry - A European Journal
VL  - 30
IS  - 25
SP  - 1-12
EP  - 1-12
PB  - Wiley
SN  - 09476539
KW  - cucurbiturils
KW  - cyclodextrins
KW  - host-guest systems
KW  - redox-active dye
UR  - https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202400535
N2  - Redox–active components are highly valuable in the construction of molecular devices. We combined two p-phenylenediamines (p-PDA) with a biphenyl (BiPhe) unit to prepare a supramolecular guest 4 consisting of three binding sites for cucurbit[7/8]uril (CBn) and/or cyclodextrins (CD). Supramolecular properties of 4 were investigated using NMR, UV-vis, mass spectrometry and isothermal titration calorimetry. Our analysis revealed that 4 forms higher–order host–guest complexes, wherein a CD unit occupies the central BiPhe site, secured by two CBn units at the terminal p-PDA sites. Additionally, 1 : 1 complexes with α-CD and β-CD, a 1 : 2 complex with γ-CD and 2 : 1 complexes with CB7 and CB8 were identified. Through UV-vis and cyclic voltammetry, redox processes leading to the formation of a stable, deep blue dication diradical of 4 are elucidated. Furthermore, it is demonstrated that CB7 selectively protects oxidised 4 from reduction in the presence of a reducing agent. The supramolecular and redox properties of the structural motif represented by 4 render it an interesting candidate for the construction of supramolecular devices.
ER  -

JANOVSKÝ, Petr; Andreas SPRINGER; Jaroslav FILIP; Zdeňka PRUCKOVÁ; Marek NEČAS; Michal ROUCHAL; Christoph A SCHALLEY a Robert VICHA. para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems. \textit{Chemistry - A European Journal}. Wiley, 2024, roč.~30, č.~25, s.~1-12. ISSN~0947-6539. Dostupné z: https://doi.org/10.1002/chem.202400535.

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